Lithium Hydroxide → HCID 71817937, compound

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Reaction Steps

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 19b (974 mg, 2.0 mmol); LiOH (47.5 mg, 2.0 mmol); THF/MeOH/H2O (25 mL: 5 mL: 2 mL); yielded 33 as a white solid (685 mg, 74.6%). 1H NMR (MeOD-d4, 400 MHz): δ 8.99-8.98 (d, 1H, J=1.67 Hz); 7.94-7.91 (q, 2H); 7.37 (s, 1H); 7.36 (s, 1H); 7.15-7.10 (t, 2H); 5.06-5.02 (q, 1H); 3.64-3.63 (d, 1H, J=1.57 Hz): 3.49-3.45 (m, 3H). 13C NMR (MeOD-d4, 100 MHz): 170.05, 169.01, 166.19, 163.43, 158.19, 154.25, 152.66, 148.36, 131.30, 128.18, 116.63, 116.15, 115.93, 108.62, 53.12, 53.05, 52.21, 33.09. ESI-HRMS (m/z): [M+H+] calcd. for C19H15FN4O5S2: 463.0541, observed: 463.0545; HPLC method 2: Rt=23.3 min; purity=96.3%.

Provenance & Evidence